Trifluoroacetic acid → 4-Chloro-2-nitro-N-(propan-2-yl)aniline

HRID 1734545Notes

Reaction equation

HRID 1734545 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.CO[C:14](OC)([CH3:16])[CH3:15].FC(F)(F)C(O)=O>C1(C)C=CC=CC=1.N1C=CC=CC=1.CCOC(C)=O.CCCCCC>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH:14]([CH3:16])[CH3:15])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

7

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 64952,2-Dimethoxypropane2×HCID 69794-Chloro-2-nitroaniline2×

Product 1

HCID 27366924-Chloro-2-nitro-N-(propan-2-yl)anilineYield 78.3%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolvent2×HCID 1140TolueneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

4-chloro-2-nitroaniline (8.6 g; 0.05 mole), 2,2-dimethoxypropane (10.0 ml; 0.9 mole) and trifluoroacetic acid [TFA] (4.0 ml; 0.005 moles) were dissolved in toluene (100 ml) and stirred for 1 hr. BH3 pyridine (5.0 ml; 0.05 moles) was added in 1.0 ml increments. The reaction was exothermic, and the reaction progress was monitored by tlc 40% EtOAc/Hexane. Additional TFA, BH3 * pyridine and 2,2-dimethoxypropane were added until the tlc indicated that the 4-chloro-2-nitroaniline was consumed. The reaction mixture was placed on a bed of silica and eluted with toluene. The product was the first major component to elute, which produced 8.4 g (78%) of a yellow crystalline solid.

Workup

  1. customwas consumed
  2. washeluted with toluene
  3. washto elute

Sources & evidence

ORD record
ord-a92897b5fa2a482fb5964c83366d34dc
Source dataset
uspto-grants-1996_07
Patent number
US05534521

Reaction notes

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